Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl
Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient
Absorption and Stimulated Raman Emission Spectroscopy

J 2022

Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy

MADEA, Dominik; Taufiqueahmed Pirsaheb MUJAWAR; Aleš DVOŘÁK; Kateřina POSPÍŠILOVÁ; Lucie MUCHOVÁ et al.

Základní údaje

Originální název

Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy

Autoři

MADEA, Dominik; Taufiqueahmed Pirsaheb MUJAWAR; Aleš DVOŘÁK; Kateřina POSPÍŠILOVÁ; Lucie MUCHOVÁ; Petra ČUBÁKOVÁ; Miroslav KLOZ; Jakub ŠVENDA; Libor VÍTEK a Petr KLÁN

Vydání

Journal of Organic Chemistry, American Chemical Society, 2022, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.600

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/22:00126178

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

Alcohols; Molecular structure; Photooxidation; Quantum mechanics; Quantum yield

Štítky

14313010, 143180, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 13. 6. 2025 10:41, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

Bilirubin (BR) is an essential metabolite formed by the catabolism of heme. Phototherapy with blue-green light can be applied to reduce high concentrations of BR in blood and is used especially in the neonatal period. In this work, we studied the photochemistry of (Z)-isovinylneoxanthobilirubic acid methyl ester, a dipyrrinone subunit of BR, by steady-state absorption, femtosecond transient absorption, and stimulated Raman spectroscopies. Both the (Z)- and (E)-configurational isomers of isovinylneoxanthobilirubic acid undergo wavelength-dependent and reversible photoisomerization. The isomerization from the excited singlet state is ultrafast (the lifetimes of (Z)- and (E)-isomers were found to be similar to 0.9 and 0.1 ps, respectively), and its efficiencies increase with increased photon energy. In addition, we studied sensitized photooxidation of the dipyrrinone subunit by singlet oxygen that leads to the formation of propentdyopents. Biological activities of these compounds, namely, effects on the superoxide production, lipoperoxidation, and tricarboxylic acid cycle metabolism, were also studied. Finally, different photochemical and biological properties of this BR subunit and its structural analogue, (Z)-vinylneoxanthobilirubic acid methyl ester, studied before, are discussed.

Návaznosti

EF16_025/0007381, projekt VaV

Název: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

NV18-07-00342, projekt VaV

Název: Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

Investor: Ministerstvo zdravotnictví ČR, Studium degradačních produktů bilirubinu vznikajících při fototerapii novorozenecké žloutenky

90121, velká výzkumná infrastruktura

Název: RECETOX RI

Citovat

MADEA, Dominik; Taufiqueahmed Pirsaheb MUJAWAR; Aleš DVOŘÁK; Kateřina POSPÍŠILOVÁ; Lucie MUCHOVÁ; Petra ČUBÁKOVÁ; Miroslav KLOZ; Jakub ŠVENDA; Libor VÍTEK a Petr KLÁN. Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy. Journal of Organic Chemistry. American Chemical Society, 2022, roč. 87, č. 5, s. 3089-3103. ISSN 0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.1c02870.

@article{1863612,
   author = {Madea, Dominik and Mujawar, Taufiqueahmed Pirsaheb and Dvořák, Aleš and Pospíšilová, Kateřina and Muchová, Lucie and Čubáková, Petra and Kloz, Miroslav and Švenda, Jakub and Vítek, Libor and Klán, Petr},
   article_number = {5},
   doi = {https://doi.org/10.1021/acs.joc.1c02870},
   keywords = {Alcohols; Molecular structure; Photooxidation; Quantum mechanics; Quantum yield},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.1c02870},
   volume = {87},
   year = {2022}
}

TY  - JOUR
ID  - 1863612
AU  - Madea, Dominik - Mujawar, Taufiqueahmed Pirsaheb - Dvořák, Aleš - Pospíšilová, Kateřina - Muchová, Lucie - Čubáková, Petra - Kloz, Miroslav - Švenda, Jakub - Vítek, Libor - Klán, Petr
PY  - 2022
TI  - Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy
JF  - Journal of Organic Chemistry
VL  - 87
IS  - 5
SP  - 3089-3103
EP  - 3089-3103
PB  - American Chemical Society
SN  - 00223263
KW  - Alcohols
KW  - Molecular structure
KW  - Photooxidation
KW  - Quantum mechanics
KW  - Quantum yield
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.1c02870
N2  - Bilirubin (BR) is an essential metabolite formed by the catabolism of heme. Phototherapy with blue-green light can be applied to reduce high concentrations of BR in blood and is used especially in the neonatal period. In this work, we studied the photochemistry of (Z)-isovinylneoxanthobilirubic acid methyl ester, a dipyrrinone subunit of BR, by steady-state absorption, femtosecond transient absorption, and stimulated Raman spectroscopies. Both the (Z)- and (E)-configurational isomers of isovinylneoxanthobilirubic acid undergo wavelength-dependent and reversible photoisomerization. The isomerization from the excited singlet state is ultrafast (the lifetimes of (Z)- and (E)-isomers were found to be similar to 0.9 and 0.1 ps, respectively), and its efficiencies increase with increased photon energy. In addition, we studied sensitized photooxidation of the dipyrrinone subunit by singlet oxygen that leads to the formation of propentdyopents. Biological activities of these compounds, namely, effects on the superoxide production, lipoperoxidation, and tricarboxylic acid cycle metabolism, were also studied. Finally, different photochemical and biological properties of this BR subunit and its structural analogue, (Z)-vinylneoxanthobilirubic acid methyl ester, studied before, are discussed.
ER  -

MADEA, Dominik; Taufiqueahmed Pirsaheb MUJAWAR; Aleš DVOŘÁK; Kateřina POSPÍŠILOVÁ; Lucie MUCHOVÁ; Petra ČUBÁKOVÁ; Miroslav KLOZ; Jakub ŠVENDA; Libor VÍTEK a Petr KLÁN. Photochemistry of (Z)-Isovinylneoxanthobilirubic Acid Methyl Ester, a Bilirubin Dipyrrinone Subunit: Femtosecond Transient Absorption and Stimulated Raman Emission Spectroscopy. \textit{Journal of Organic Chemistry}. American Chemical Society, 2022, roč.~87, č.~5, s.~3089-3103. ISSN~0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.1c02870.

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